As part of a broad program concerning the total synthesis of biologically-active natural products and analogs not found in nature, we have initiated studies directed toward the synthesis of sesquiterpene alpha-methylene-gamma-lactones and cyclic biphenyls and anthracyclines. The lactones are important targets for practical synthesis because members of this family display considerable biological activity as allergenic agents, growth inhibitors, antibacterial agents, and antitumor agents. Cyclic biphenyl such as steganacin are known antileukemia and antitumor agents, while a related structural family, the alnusones, has not been tested for biological activity. We will prepare aklavanone, the aglycone of aclacinomycin, another promising antitumor drug with a structure closely related to adriamycin. We have shown the feasibility of a new strategy for alpha-methylene-gamma-lactone synthesis and will apply the method to the total synthesis of confertin, and related natural products. New methods are proposed and, after preliminary studies on the model systems, will be applied in total synthesis. The new methods involve organo-transition metal intermediates.